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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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Based on their attached substituent groups, ethers can be classified into two...

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Updated: Jun 9, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

(E)-4-Chloro-2-[(4-hy-droxy-3-meth-oxy-benzyl-idene)amino]-phenol.

Amel Marir1, Yamina Boudinar2,3, Ouafa Boukhemis4,5

  • 1Faculté des Sciences Exacte, Université des Fréres Mentouri-Constantine 1, Algeria.

Iucrdata
|June 8, 2026
PubMed
Summary
This summary is machine-generated.

A novel compound was synthesized from 2-amino-4-chloro phenol and vanillin. Structural analysis revealed two distinct molecular conformations and an intricate three-dimensional network stabilized by various intermolecular interactions.

Keywords:
Schiff basecrystal structurehydrogen bondingvanillin

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Published on: August 19, 2013

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Schiff bases are versatile compounds with diverse applications.
  • Vanillin derivatives are of interest due to their biological and chemical properties.

Purpose of the Study:

  • To synthesize and characterize a novel Schiff base derived from vanillin.
  • To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • The synthesis involved the reaction of 2-amino-4-chloro phenol with vanillin.

Main Results:

  • The title compound, C14H12ClNO3, crystallizes with two conformationally distinct molecules in the asymmetric unit.
  • Intramolecular hydrogen bonds (O-H⋯O, O-H⋯N) forming S(5) ring motifs were observed in both molecules.
  • The extended crystal structure features a 3D network stabilized by O-H⋯O, C-H⋯Cl, C-H⋯O hydrogen bonds, and C-H⋯π/π-π interactions.

Conclusions:

  • The study successfully synthesized and characterized a novel vanillin-derived Schiff base.
  • The crystal structure reveals complex intermolecular interactions contributing to a 3D network.
  • The findings provide insights into the structural diversity and supramolecular assembly of Schiff base compounds.